On 29 April 1789 he was caught stealing food. Two weeks later he escaped into the bush, taking food, an iron cooking pot, and a musket (gun) taken from a sea army officer (Marine) named Abraham Hand. He could not catch enough animals to eat, and he began to steal food from the settlement. On 26 May he stole food from a brick making gang at Brickfield Hill and was nearly caught. On June 6 he tried to steal food from Zachariah Clark, who was the assistant in charge of the new colony's food supplies. Caesar was caught by a convict named William Saltmarsh.

In July 1789, David Collins, the colony's Judge-Advocate, said that John Caesar was the hardest working convict in the new colony.[3] He said that he was a large man with a lot of muscles, but he was always hungry. He would eat food meant to last two days in one meal, and would then need to steal more food from others. All his thefts were about getting more food.

After he was captured, Collins said Caesar was a "wretch" (a miserable person) who did not care if he died. Caesar told Collins that he would make it if was hanged, he would turn into a joke by playing a trick on the executioner. Governor Arthur Phillip however, thought Caesar would be more use working and sent him to Garden Island, where he would work in with his legs tied with iron chain. He was well behaved and the chains were soon taken off.

Caesar soon escaped again; on 22 December used a canoe to get off the island, taking a week's worth of food. He stole a musket, and lived by taking food from gardens and taking the food of Aboriginals after scaring them away with his gun. After he lost the gun at Rose Hill, and was attacked by the Aborigines, leaving him wounded in several places. He gave himself up on the 31 December to an officer at Rose Hill.

On 6 March 1790, Caesar was sent to Norfolk Island. There he had one daughter, later named Mary Ann Fisher Power, to Ann (e) Power. He was taken back to Sydney in 1793, and began stealing from the farms and huts again. He was caught and then flogged (hit 500 times with a whip).[1] This did not make any difference; Caesar said that "all that would not make him better."

In 1795 Black Caesar ran away for the last time, and formed a gang of runaways. On 29 January 1796, a reward of five gallons of rum was offered by Governor John Hunter for his capture. Every day there were reports of missing things, but he was able to avoid being captured until 15 February. A man named Wimbow, who had been searching for days, found him in an area of thick bush called Liberty Plains and shot him.[1] He died soon after.